Pigment compositions

Abstract

Disclosed are compositions comprising one or more compounds characterized by the formula: ##STR1## wherein Ar is an aromatic moiety having at least one substituent which is an acid group or salt thereof; X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a is 1, 2 or 3. Also disclosed is a process for preparing azo dyes which comprises coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts thereof; with (ii) at least one coupling component represented by the formula: ##STR2## wherein X, Y and a are as defined above. The dye compositions prepared by this process and the azo pigments derived from such dyes are also disclosed. Paint, ink and plastic compositions containing the foregoing pigments compositions are disclosed.

What is claimed is: 
     
       1. An azo pigment composition comprising one or more compounds of the formula: ##STR8## wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; a equals 1, 2 or 3; and Ar is an aromatic moiety having as a substituent a divalent metal salt of a carboxylic acid or sulfonic acid group, provided that when Ar is monocyclic it is of the formula: ##STR9## wherein each Z is independently a salt of a --COOH or --SO 3  H group; m is 1 or 2; each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and n is 0, 1 or 2. 
     
     
       2. A composition according to claim 1 wherein Z is a sulfonic acid salt of a divalent metal selected from the group consisting of alkaline earth metals, manganese, nickel and zinc. 
     
     
       3. A composition according to claim 1 wherein X and Y are each lower alkyl groups and a equals 1. 
     
     
       4. A composition according to claim 3 wherein X and Y are methyl groups. 
     
     
       5. A composition according to claim 1 wherein n equals 1; R is a methyl, or chloro group. 
     
     
       6. A process for preparing an azo pigment which comprises forming a dye by coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts of such groups wherein the aromatic amines are selected from the group consisting of fused cyclic aromatic amines or aromatic amines of the formula: ##STR10## wherein each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; n is equal to 0, 1 or 2; each Z is independently a --COOH or --SO 3  H group, or salts of such groups; and m is equal to 1 or 2; with (ii) at least one coupling component of the formula: ##STR11## wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a equals 1, 2 or 3; and metallizing said dye with at least one divalent metal. 
     
     
       7. A process according to claim 6 wherein X and Y are lower alkyl groups and a equals 1. 
     
     
       8. A process according to claim 6 wherein X and Y are methyl groups, a equals 1; R is a methyl or chloro group; n equals 1; Z is a --SO 3  H group or salt thereof and m equals 1. 
     
     
       9. A process wherein the azo dye prepared according to claim 6 is metallized with one or more of alkaline earth metals, manganese, nickel or zinc. 
     
     
       10. A composition prepared according to the process of claim 6. 
     
     
       11. A composition prepared according to the process of claim 9. 
     
     
       12. A paint composition comprising a paint vehicle and the composition of claim 1. 
     
     
       13. A paint composition comprising a paint vehicle and the composition of claim 10. 
     
     
       14. An ink composition comprising an ink vehicle and the composition of claim 1. 
     
     
       15. An ink composition comprising an ink vehicle and the composition of claim 10. 
     
     
       16. A plastic composition comprising a plastic material and the composition of claim 1. 
     
     
       17. A plastic composition comprising a plastic material and the composition of claim 10.